# Supplementary Material (ESI) for New Journal of Chemistry # This journal is (c) The Royal Society of Chemistry and # The Centre National de la Recherche Scientifique, 2007 data_global _journal_name_full 'New J.Chem.(Nouv.J.Chim.)' _journal_coden_Cambridge 0440 #=================================================================== _audit_creation_date 11-Nov-03 _audit_creation_method 'PLATON option' _audit_update_record ; 11-Nov-03 Updated by the Author E.H. Text writing by E.H. Checkcif OK 22-Nov-06 Updated by the Author E.H. ; _publ_contact_author_name 'Franz Schmidtchen' _publ_contact_author_address ; Chemistry Technical University of Munich Lichtenbergstrasse 4 Garching 85747 GERMANY ; _publ_contact_author_email SCHMIDTCHEN@CH.TUM.DE _publ_section_title ; Sulfoniumcalixpyrrole: The decoration of a calix[4]pyrrole host with positive charges boosts affinity and selectivity of anion binding in DMSO solvent ; _publ_section_abstract ; With the goal to improve host-guest binding affinity while... ; # Insert blank lines between paragraphs _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M. C., Polidori, G. & Camalli, M. (1994). SIR92, J. Appl. Cryst. 27, 435-436. Farrugia, L. J. (1999). WinGX (Version 1.70.01 January 2005), J. Appl. Cryst. 32, 837-838. Nonius (2001a). Data Collection Software for Nonius Kappa-CCD devices. Nonius BV, Delft, The Netherlands. Nonius (2001b). DENZO Processing Software for Nonius Kappa-CCD devices, Nonius BV, Delft, The Netherlands. Sheldrick, G. M. (1998). SHELXL97, University of G\"ottingen, G\"ottingen, Germany. Spek, A. L. (2006). PLATON, A Multipurpose Crystallographic Tool, Utrecht University, Utrecht, The Netherlands. ; loop_ _publ_author_name F.Schmidtchen E.Herdtweck V.Kral M.Valik #=================================================================== data_VALA-4209-173 _database_code_depnum_ccdc_archive 'CCDC 632829' #=================================================================== _chemical_name_systematic ; ; _chemical_name_common ? _chemical_formula_moiety 'C36 H44 N4 S4, 2(C3 H6 O)' _chemical_formula_structural ? _chemical_formula_analytical ? _chemical_formula_sum 'C42 H56 N4 O2 S4' _chemical_formula_weight 777.19 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_Hall '-P 2ac 2ab' _symmetry_space_group_name_H-M 'P b c a' _symmetry_Int_Tables_number 61 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,-y,1/2+z 1/2+x,1/2-y,-z -x,1/2+y,1/2-z -x,-y,-z 1/2+x,y,1/2-z 1/2-x,1/2+y,z x,1/2-y,1/2+z _cell_length_a 16.0948(1) _cell_length_b 26.2675(1) _cell_length_c 19.2980(1) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 8158.62(7) _cell_formula_units_Z 8 _cell_measurement_temperature 173(1) _cell_measurement_reflns_used 8205 _cell_measurement_theta_min 1.55 _cell_measurement_theta_max 25.36 _exptl_crystal_description fragment _exptl_crystal_colour colorless _exptl_crystal_size_max 0.33 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas none _exptl_crystal_density_diffrn 1.265 _exptl_crystal_density_method none _exptl_crystal_F_000 3328 _exptl_absorpt_coefficient_mu 0.274 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.910 _exptl_absorpt_correction_T_max 0.926 _exptl_absorpt_process_details '(applied during the scaling procedure; Nonius, 2001b)' _exptl_special_details ; Diffractometer operator E. Herdtweck scanspeed 2 x 15 s per film repetition 1 dx 40 936 films measured in 7 data sets set 1: phi-scan with delta_phi = 1.0 set 2 to 7: omega-scans with delta_omega = 1.0 ; _publ_section_exptl_prep ; The crystal was fixed in a capillary with perfluorinated ether and transferred to the diffractometer. ; _publ_section_exptl_refinement ; Solution and refinements with the program WinGX; Farrugia (1999). Hydrogen atoms could be located in the difference Fourier maps and were allowed to refine freely, whereas the hydogen positions of the solvent molecules were calculated in ideal positions (riding model). ; _diffrn_ambient_temperature 173(1) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_source 'NONIUS FR 591 rotating anode' _diffrn_radiation_monochromator graphite _diffrn_measurement_device ' \k-geometry diffractometer ' _diffrn_measurement_device_type ' Nonius \k-CCD diffractometer' _diffrn_measurement_method ' phi- and omega-rotation ' _diffrn_detector ' CCD plate ' _diffrn_detector_area_resol_mean 18 # 9 for binned mode _diffrn_standards_decay_% 0 # number of measured reflections (redundant set) _diffrn_reflns_number 152651 _diffrn_reflns_av_R_equivalents 0.044 _diffrn_reflns_av_sigmaI/netI 0.0160 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_h_max 19 _diffrn_reflns_limit_k_min -31 _diffrn_reflns_limit_k_max 31 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_theta_min 1.55 _diffrn_reflns_theta_max 25.36 _reflns_number_total 7476 _reflns_number_gt 6473 # number of observed reflections (> n sig(I)) _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Kappa-CCD Control Software (Nonius, 2001a)' _computing_cell_refinement 'DENZO (Nonius, 2001b)' _computing_data_reduction 'DENZO (Nonius, 2001b)' _computing_structure_solution 'SIR92 (Altomare, 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1998)' _computing_molecular_graphics 'PLATON (Spek, 2006)' _computing_publication_material 'PLATON (Spek, 2006)' _refine_special_details ; Refinement on F^2^ for ALL reflections except for 0 with very negative F^2^ or flagged by the user for potential systematic errors. Weighted R-factors wR and all goodnesses of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The observed criterion of F^2^ > 2sigma(F^2^) is used only for calculating R_factor_obs etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Referee B, point 1: There is a short intramolecular contact between unit-occupancy H531 acetone and H452 of another disordered (0.131 occ.) acetone molecule. A critical inspection of the ADP's of the C53 atom indicates unusual behavior (U3/U1=6.53). Attempts to refine a split-model of Atom C53 failed. But it is clear that with such a split-model the observed short contact will disappear. Referee B, point 3: The disorder model was refined with the usual SHELX-97 procedure: TITL VALA 4209-173... ... EXYZ C431 C432 EADP C431 C432 ... FVAR 0.20303 0.86887 ... PART 1 C41 1 0.02548 0.17709 0.34568 21.00000 0.04071 0.07229 = 0.04508 0.00391 0.01069 0.00689 AFIX 37 H411 2 -0.01969 0.20048 0.35776 21.00000 -1.50000 H412 2 0.01202 0.15961 0.30224 21.00000 -1.50000 H413 2 0.07719 0.19633 0.33999 21.00000 -1.50000 AFIX 0 C42 1 0.03594 0.13891 0.40192 21.00000 0.03219 0.05919 = 0.03347 -0.00902 -0.00204 0.00848 C431 1 0.10100 0.10053 0.39128 21.00000 0.07150 0.10332 = 0.06319 -0.00934 0.00385 0.03647 AFIX 37 H431 2 0.09797 0.07497 0.42818 21.00000 -1.50000 H432 2 0.15560 0.11703 0.39227 21.00000 -1.50000 H433 2 0.09287 0.08398 0.34628 21.00000 -1.50000 AFIX 0 PART 2 C432 1 0.10100 0.10053 0.39128 -21.00000 0.07150 0.10332 = 0.06319 -0.00934 0.00385 0.03647 AFIX 37 H434 2 0.09573 0.06685 0.36988 -21.00000 -1.50000 H435 2 0.15214 0.10188 0.41878 -21.00000 -1.50000 H436 2 0.10304 0.12662 0.35501 -21.00000 -1.50000 AFIX 0 C44 1 0.03609 0.10900 0.43213 -21.00000 0.03413 0.06742 = 0.05741 -0.03566 -0.01018 0.03096 C45 1 0.02651 0.05442 0.44669 -21.00000 0.07504 0.07498 = 0.08395 -0.04221 -0.00635 0.01717 AFIX 37 H451 2 0.07598 0.04190 0.47089 -21.00000 -1.50000 H452 2 0.01972 0.03584 0.40302 -21.00000 -1.50000 H453 2 -0.02257 0.04911 0.47586 -21.00000 -1.50000 AFIX 0 PART 0 ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme sigma _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(Fo^2^)+(0.0424P)^2^+5.4301P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_number_reflns 7476 _refine_ls_number_parameters 670 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0432 _refine_ls_R_factor_gt 0.0354 _refine_ls_wR_factor_ref 0.0908 _refine_ls_wR_factor_gt 0.0859 _refine_ls_goodness_of_fit_ref 1.016 _refine_ls_restrained_S_all 1.016 _refine_ls_shift/su_max 0.084 _refine_ls_shift/su_mean 0.000 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 25.36 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.393 _refine_diff_density_min -0.445 _refine_diff_density_rms 0.042 loop_ _atom_site_label _atom_site_type_symbol _atom_site_thermal_displace_type _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_occupancy _atom_site_U_iso_or_equiv _atom_site_calc_flag _atom_site_refinement_flags S1 S Uani 0.19061(3) 0.38997(2) 0.07074(2) 1.000 0.0354(2) . . S2 S Uani 0.04394(3) 0.56831(2) 0.31661(3) 1.000 0.0431(2) . . S3 S Uani 0.21236(3) 0.32264(2) 0.74461(2) 1.000 0.0353(2) . . S4 S Uani 0.46284(3) 0.15612(2) 0.51091(3) 1.000 0.0404(2) . . N1 N Uani 0.21644(8) 0.41988(5) 0.30271(7) 1.000 0.0200(4) . . N2 N Uani 0.19176(9) 0.41791(5) 0.48609(7) 1.000 0.0251(4) . . N3 N Uani 0.31952(8) 0.30798(5) 0.50621(7) 1.000 0.0206(4) . . N4 N Uani 0.31256(8) 0.30017(5) 0.32311(7) 1.000 0.0212(4) . . C1 C Uani 0.20181(9) 0.37438(6) 0.26937(8) 1.000 0.0200(4) . . C2 C Uani 0.12495(10) 0.35807(6) 0.29020(8) 1.000 0.0243(5) . . C3 C Uani 0.09219(10) 0.39482(6) 0.33676(9) 1.000 0.0249(5) . . C4 C Uani 0.14990(10) 0.43279(6) 0.34351(8) 1.000 0.0205(4) . . C5 C Uani 0.15313(10) 0.47847(6) 0.39154(8) 1.000 0.0231(4) . . C6 C Uani 0.20409(10) 0.46392(6) 0.45412(8) 1.000 0.0240(5) . . C7 C Uani 0.26473(12) 0.48841(7) 0.49085(9) 1.000 0.0322(6) . . C8 C Uani 0.28905(12) 0.45629(7) 0.54638(9) 1.000 0.0313(5) . . C9 C Uani 0.24326(10) 0.41268(6) 0.54233(8) 1.000 0.0236(5) . . C10 C Uani 0.23791(10) 0.36530(6) 0.58663(8) 1.000 0.0219(5) . . C11 C Uani 0.24589(10) 0.31952(6) 0.53913(7) 1.000 0.0198(4) . . C12 C Uani 0.18792(10) 0.28611(6) 0.51499(8) 1.000 0.0244(5) . . C13 C Uani 0.22700(10) 0.25305(6) 0.46690(9) 1.000 0.0250(5) . . C14 C Uani 0.30896(9) 0.26715(6) 0.46212(8) 1.000 0.0196(4) . . C15 C Uani 0.37827(9) 0.24646(6) 0.41711(8) 1.000 0.0203(4) . . C16 C Uani 0.38036(9) 0.27485(6) 0.34848(8) 1.000 0.0220(5) . . C17 C Uani 0.44168(11) 0.27954(7) 0.29962(9) 1.000 0.0302(5) . . C18 C Uani 0.40950(11) 0.30879(7) 0.24376(9) 1.000 0.0305(5) . . C19 C Uani 0.32922(10) 0.32136(6) 0.25961(8) 1.000 0.0220(5) . . C20 C Uani 0.26408(9) 0.35123(6) 0.21958(8) 1.000 0.0209(4) . . C21 C Uani 0.21856(11) 0.31435(6) 0.16963(9) 1.000 0.0261(5) . . C22 C Uani 0.15191(12) 0.33892(7) 0.12469(9) 1.000 0.0308(5) . . C23 C Uani 0.24928(12) 0.42552(7) 0.13450(9) 1.000 0.0309(5) . . C24 C Uani 0.30824(10) 0.39266(7) 0.17640(9) 1.000 0.0247(5) . . C25 C Uani 0.19424(12) 0.52493(6) 0.35680(9) 1.000 0.0276(5) . . C26 C Uani 0.14713(13) 0.54584(7) 0.29512(10) 1.000 0.0356(6) . . C27 C Uani 0.00608(12) 0.51153(7) 0.35936(11) 1.000 0.0372(6) . . C28 C Uani 0.06402(11) 0.49276(7) 0.41598(9) 1.000 0.0302(5) . . C29 C Uani 0.15229(11) 0.36596(6) 0.62302(9) 1.000 0.0254(5) . . C30 C Uani 0.13758(11) 0.32323(7) 0.67453(9) 1.000 0.0294(5) . . C31 C Uani 0.30531(11) 0.32243(7) 0.69199(9) 1.000 0.0305(5) . . C32 C Uani 0.30779(11) 0.36655(7) 0.64103(9) 1.000 0.0269(5) . . C33 C Uani 0.46288(10) 0.25285(7) 0.45384(9) 1.000 0.0253(5) . . C34 C Uani 0.46831(11) 0.22421(8) 0.52236(9) 1.000 0.0326(6) . . C35 C Uani 0.36536(12) 0.15473(7) 0.46439(10) 1.000 0.0328(6) . . C36 C Uani 0.36383(11) 0.18927(6) 0.40138(9) 1.000 0.0259(5) . . O40 O Uani -0.00829(10) 0.13958(7) 0.45377(8) 1.000 0.0556(5) . . C41 C Uani 0.02548(16) 0.17709(11) 0.34568(13) 0.869(4) 0.0527(9) . . C42 C Uani 0.03594(15) 0.13891(13) 0.40192(14) 0.869(4) 0.0416(8) . . C431 C Uani 0.10101(19) 0.10054(13) 0.39128(15) 0.869(4) 0.0792(11) . . C45 C Uani 0.0265(14) 0.0544(8) 0.4467(12) 0.131(4) 0.078(9) . . C432 C Uani 0.10101(19) 0.10054(13) 0.39128(15) 0.131(4) 0.0792(11) . . C44 C Uani 0.0361(10) 0.1090(9) 0.4321(12) 0.131(4) 0.053(7) . . O50 O Uani 0.38098(8) 0.46986(5) 0.30942(7) 1.000 0.0374(4) . . C51 C Uani 0.43441(11) 0.45082(7) 0.34502(10) 1.000 0.0350(6) . . C52 C Uani 0.41794(14) 0.40695(8) 0.39165(11) 1.000 0.0456(7) . . C53 C Uani 0.52168(15) 0.46926(13) 0.33959(19) 1.000 0.0933(15) . . H1 H Uiso 0.2620(13) 0.4356(8) 0.3021(10) 1.000 0.033(5) . . H2 H Uiso 0.1610(12) 0.3955(8) 0.4730(10) 1.000 0.032(5) . . H3 H Uiso 0.3657(12) 0.3243(7) 0.5128(9) 1.000 0.026(5) . . H4 H Uiso 0.2686(12) 0.3030(7) 0.3439(10) 1.000 0.029(5) . . H21 H Uiso 0.0969(11) 0.3281(7) 0.2739(9) 1.000 0.026(4) . . H31 H Uiso 0.0419(12) 0.3930(7) 0.3589(10) 1.000 0.028(5) . . H71 H Uiso 0.2868(12) 0.5206(8) 0.4796(10) 1.000 0.037(5) . . H81 H Uiso 0.3296(13) 0.4628(8) 0.5801(11) 1.000 0.041(6) . . H121 H Uiso 0.1318(13) 0.2848(7) 0.5279(10) 1.000 0.034(5) . . H131 H Uiso 0.2011(11) 0.2259(7) 0.4440(9) 1.000 0.029(5) . . H171 H Uiso 0.4959(13) 0.2656(8) 0.3026(10) 1.000 0.041(5) . . H181 H Uiso 0.4372(13) 0.3189(8) 0.2037(11) 1.000 0.042(6) . . H211 H Uiso 0.2613(12) 0.2985(7) 0.1398(9) 1.000 0.030(5) . . H212 H Uiso 0.1950(11) 0.2865(7) 0.1960(9) 1.000 0.025(4) . . H221 H Uiso 0.1061(12) 0.3513(7) 0.1530(9) 1.000 0.028(5) . . H222 H Uiso 0.1299(13) 0.3153(8) 0.0924(11) 1.000 0.044(6) . . H231 H Uiso 0.2816(13) 0.4515(8) 0.1064(11) 1.000 0.044(6) . . H232 H Uiso 0.2088(12) 0.4431(7) 0.1649(10) 1.000 0.030(5) . . H241 H Uiso 0.3419(11) 0.4140(7) 0.2077(9) 1.000 0.027(5) . . H242 H Uiso 0.3455(11) 0.3764(6) 0.1447(9) 1.000 0.024(4) . . H251 H Uiso 0.1981(11) 0.5506(7) 0.3924(9) 1.000 0.027(5) . . H252 H Uiso 0.2513(12) 0.5159(7) 0.3425(9) 1.000 0.030(5) . . H261 H Uiso 0.1437(12) 0.5208(8) 0.2590(11) 1.000 0.040(5) . . H262 H Uiso 0.1771(13) 0.5752(8) 0.2753(10) 1.000 0.042(6) . . H271 H Uiso -0.0037(12) 0.4853(8) 0.3241(10) 1.000 0.036(5) . . H272 H Uiso -0.0463(14) 0.5213(8) 0.3780(11) 1.000 0.045(6) . . H281 H Uiso 0.0380(12) 0.4631(8) 0.4398(10) 1.000 0.034(5) . . H282 H Uiso 0.0700(12) 0.5200(8) 0.4522(10) 1.000 0.035(5) . . H291 H Uiso 0.1485(11) 0.3983(7) 0.6472(10) 1.000 0.029(5) . . H292 H Uiso 0.1074(11) 0.3653(7) 0.5887(9) 1.000 0.024(4) . . H301 H Uiso 0.1399(11) 0.2904(7) 0.6522(10) 1.000 0.030(5) . . H302 H Uiso 0.0832(13) 0.3269(7) 0.6968(10) 1.000 0.036(5) . . H311 H Uiso 0.3498(13) 0.3253(8) 0.7242(11) 1.000 0.040(5) . . H312 H Uiso 0.3092(12) 0.2888(8) 0.6672(10) 1.000 0.038(5) . . H321 H Uiso 0.3025(11) 0.3976(7) 0.6659(9) 1.000 0.026(5) . . H322 H Uiso 0.3625(12) 0.3671(7) 0.6167(10) 1.000 0.032(5) . . H331 H Uiso 0.5073(11) 0.2410(6) 0.4236(9) 1.000 0.021(4) . . H332 H Uiso 0.4755(11) 0.2893(7) 0.4613(9) 1.000 0.028(5) . . H341 H Uiso 0.5220(13) 0.2306(7) 0.5437(10) 1.000 0.036(5) . . H342 H Uiso 0.4238(12) 0.2353(7) 0.5536(10) 1.000 0.032(5) . . H351 H Uiso 0.3210(12) 0.1639(7) 0.4960(10) 1.000 0.035(5) . . H352 H Uiso 0.3587(14) 0.1193(9) 0.4510(11) 1.000 0.050(6) . . H361 H Uiso 0.4054(11) 0.1788(6) 0.3692(9) 1.000 0.025(4) . . H362 H Uiso 0.3102(12) 0.1850(7) 0.3783(10) 1.000 0.030(5) . . H413 H Uiso 0.07720 0.19630 0.34000 0.869(4) 0.0790 calc R H432 H Uiso 0.15560 0.11700 0.39270 0.869(4) 0.1190 calc R H433 H Uiso 0.09320 0.08420 0.34610 0.869(4) 0.1190 calc R H431 H Uiso 0.09770 0.07480 0.42790 0.869(4) 0.1190 calc R H411 H Uiso -0.01970 0.20050 0.35780 0.869(4) 0.0790 calc R H412 H Uiso 0.01200 0.15960 0.30220 0.869(4) 0.0790 calc R H434 H Uiso 0.09310 0.06840 0.36640 0.131(4) 0.1190 calc R H435 H Uiso 0.15160 0.09850 0.41940 0.131(4) 0.1190 calc R H436 H Uiso 0.10630 0.12840 0.35780 0.131(4) 0.1190 calc R H451 H Uiso 0.07590 0.04190 0.47090 0.131(4) 0.1170 calc R H452 H Uiso 0.01960 0.03580 0.40310 0.131(4) 0.1170 calc R H453 H Uiso -0.02260 0.04910 0.47590 0.131(4) 0.1170 calc R H521 H Uiso 0.35850 0.40560 0.40270 1.000 0.0680 calc R H522 H Uiso 0.44990 0.41100 0.43450 1.000 0.0680 calc R H523 H Uiso 0.43450 0.37530 0.36850 1.000 0.0680 calc R H531 H Uiso 0.54270 0.47750 0.38590 1.000 0.1400 calc R H532 H Uiso 0.52340 0.49980 0.31040 1.000 0.1400 calc R H533 H Uiso 0.55630 0.44260 0.31880 1.000 0.1400 calc R loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0380(3) 0.0453(3) 0.0229(2) 0.0030(2) -0.0030(2) 0.0093(2) S2 0.0528(3) 0.0271(2) 0.0495(3) 0.0048(2) -0.0087(2) 0.0104(2) S3 0.0410(3) 0.0452(3) 0.0197(2) 0.0033(2) -0.0003(2) 0.0052(2) S4 0.0408(3) 0.0443(3) 0.0360(3) 0.0140(2) 0.0044(2) 0.0180(2) N1 0.0189(7) 0.0195(7) 0.0215(7) -0.0018(5) 0.0001(5) -0.0011(6) N2 0.0319(8) 0.0186(7) 0.0247(7) -0.0008(6) -0.0046(6) -0.0048(6) N3 0.0183(7) 0.0206(7) 0.0229(7) -0.0025(5) 0.0001(5) -0.0022(6) N4 0.0174(7) 0.0239(7) 0.0222(7) 0.0003(5) 0.0026(5) 0.0028(6) C1 0.0212(8) 0.0188(7) 0.0200(8) 0.0002(6) -0.0021(6) 0.0014(6) C2 0.0233(8) 0.0219(8) 0.0276(8) -0.0037(7) 0.0010(7) -0.0037(7) C3 0.0214(8) 0.0261(8) 0.0273(8) 0.0002(7) 0.0059(7) -0.0011(7) C4 0.0235(8) 0.0201(7) 0.0179(7) 0.0008(6) 0.0012(6) 0.0027(6) C5 0.0285(8) 0.0184(7) 0.0224(8) -0.0013(6) 0.0033(7) 0.0022(7) C6 0.0317(9) 0.0188(8) 0.0214(8) -0.0022(6) 0.0043(7) 0.0008(7) C7 0.0449(11) 0.0238(9) 0.0278(9) -0.0014(7) -0.0005(8) -0.0093(8) C8 0.0386(10) 0.0298(9) 0.0255(9) -0.0033(7) -0.0063(8) -0.0073(8) C9 0.0290(8) 0.0230(8) 0.0189(8) -0.0036(6) -0.0006(7) 0.0019(7) C10 0.0242(8) 0.0218(8) 0.0196(8) -0.0022(6) -0.0026(6) 0.0021(6) C11 0.0202(7) 0.0219(8) 0.0172(7) 0.0002(6) 0.0005(6) 0.0038(6) C12 0.0165(8) 0.0308(9) 0.0259(8) -0.0049(7) 0.0017(6) -0.0005(7) C13 0.0212(8) 0.0262(8) 0.0275(8) -0.0070(7) 0.0000(7) -0.0034(7) C14 0.0201(8) 0.0191(7) 0.0195(7) -0.0014(6) -0.0008(6) 0.0008(6) C15 0.0177(7) 0.0224(8) 0.0209(7) -0.0004(6) 0.0006(6) 0.0015(6) C16 0.0198(8) 0.0231(8) 0.0231(8) -0.0002(6) -0.0015(6) 0.0025(6) C17 0.0213(8) 0.0380(10) 0.0313(9) 0.0066(8) 0.0044(7) 0.0089(7) C18 0.0268(9) 0.0400(10) 0.0248(9) 0.0069(8) 0.0061(7) 0.0065(8) C19 0.0230(8) 0.0227(8) 0.0203(8) -0.0005(6) 0.0011(6) 0.0013(6) C20 0.0204(8) 0.0222(8) 0.0202(7) -0.0004(6) 0.0004(6) 0.0025(6) C21 0.0303(9) 0.0233(8) 0.0248(8) -0.0051(7) -0.0012(7) 0.0031(7) C22 0.0313(9) 0.0346(10) 0.0264(9) -0.0054(8) -0.0062(8) 0.0016(8) C23 0.0324(9) 0.0313(9) 0.0290(9) 0.0049(8) 0.0022(8) 0.0044(8) C24 0.0236(8) 0.0284(9) 0.0221(8) 0.0014(7) 0.0020(7) 0.0023(7) C25 0.0374(10) 0.0191(8) 0.0262(9) 0.0001(7) 0.0024(7) -0.0008(7) C26 0.0495(12) 0.0260(9) 0.0312(10) 0.0050(8) 0.0008(9) -0.0010(9) C27 0.0337(10) 0.0316(10) 0.0464(11) -0.0009(9) 0.0030(9) 0.0100(8) C28 0.0352(10) 0.0257(9) 0.0296(9) -0.0013(7) 0.0094(8) 0.0064(8) C29 0.0271(9) 0.0270(9) 0.0220(8) -0.0026(7) 0.0012(7) 0.0060(7) C30 0.0291(9) 0.0362(10) 0.0228(8) 0.0016(7) 0.0028(7) 0.0040(8) C31 0.0313(9) 0.0360(10) 0.0243(9) -0.0007(8) -0.0048(7) 0.0052(8) C32 0.0304(9) 0.0296(9) 0.0207(8) -0.0063(7) -0.0042(7) 0.0005(7) C33 0.0168(8) 0.0340(10) 0.0252(8) -0.0001(7) 0.0006(7) 0.0022(7) C34 0.0232(9) 0.0498(11) 0.0247(9) 0.0013(8) -0.0019(7) 0.0079(8) C35 0.0396(10) 0.0231(9) 0.0356(10) 0.0009(8) 0.0053(8) 0.0039(8) C36 0.0293(9) 0.0232(8) 0.0251(8) -0.0040(7) 0.0031(7) 0.0043(7) O40 0.0521(9) 0.0739(11) 0.0407(8) -0.0014(8) 0.0089(7) 0.0138(9) C41 0.0407(14) 0.0723(19) 0.0451(15) 0.0039(13) 0.0107(11) 0.0069(13) C42 0.0322(12) 0.0592(18) 0.0335(13) -0.0090(12) -0.0020(10) 0.0085(12) C431 0.0715(18) 0.103(2) 0.0632(17) -0.0093(16) 0.0038(15) 0.0365(17) C45 0.075(15) 0.075(15) 0.084(16) -0.042(12) -0.006(12) 0.017(11) C432 0.0715(18) 0.103(2) 0.0632(17) -0.0093(16) 0.0038(15) 0.0365(17) C44 0.034(9) 0.068(14) 0.058(13) -0.036(11) -0.010(8) 0.031(9) O50 0.0292(7) 0.0387(7) 0.0442(7) 0.0032(6) -0.0039(6) -0.0031(6) C51 0.0289(9) 0.0353(10) 0.0407(10) 0.0002(8) 0.0002(8) 0.0002(8) C52 0.0485(12) 0.0403(11) 0.0479(12) 0.0056(9) -0.0063(10) -0.0041(10) C53 0.0350(13) 0.112(3) 0.133(3) 0.066(2) -0.0216(16) -0.0191(15) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_publ_flag S1 C22 1.8083(19) . . yes S1 C23 1.8104(19) . . yes S2 C26 1.811(2) . . yes S2 C27 1.810(2) . . yes S3 C30 1.8105(18) . . yes S3 C31 1.8081(18) . . yes S4 C34 1.804(2) . . yes S4 C35 1.808(2) . . yes O40 C42 1.228(3) . . yes O40 C44 1.15(2) . . yes O50 C51 1.209(2) . . yes N1 C1 1.378(2) . . yes N1 C4 1.372(2) . . yes N2 C6 1.371(2) . . yes N2 C9 1.373(2) . . yes N3 C14 1.380(2) . . yes N3 C11 1.378(2) . . yes N4 C16 1.369(2) . . yes N4 C19 1.372(2) . . yes N1 H1 0.84(2) . . no N2 H2 0.81(2) . . no N3 H3 0.867(19) . . no N4 H4 0.817(19) . . no C1 C2 1.369(2) . . no C1 C20 1.516(2) . . no C2 C3 1.420(2) . . no C3 C4 1.369(2) . . no C4 C5 1.517(2) . . no C5 C28 1.556(2) . . no C5 C25 1.542(2) . . no C5 C6 1.509(2) . . no C6 C7 1.367(2) . . no C7 C8 1.419(3) . . no C8 C9 1.364(2) . . no C9 C10 1.512(2) . . no C10 C29 1.547(2) . . no C10 C11 1.518(2) . . no C10 C32 1.539(2) . . no C11 C12 1.363(2) . . no C12 C13 1.418(2) . . no C13 C14 1.373(2) . . no C14 C15 1.515(2) . . no C15 C33 1.544(2) . . no C15 C36 1.550(2) . . no C15 C16 1.520(2) . . no C16 C17 1.371(2) . . no C17 C18 1.421(3) . . no C18 C19 1.368(2) . . no C19 C20 1.520(2) . . no C20 C21 1.551(2) . . no C20 C24 1.544(2) . . no C21 C22 1.523(3) . . no C23 C24 1.516(3) . . no C25 C26 1.514(3) . . no C27 C28 1.519(3) . . no C29 C30 1.518(2) . . no C31 C32 1.520(3) . . no C33 C34 1.524(3) . . no C35 C36 1.517(3) . . no C2 H21 0.960(18) . . no C3 H31 0.917(19) . . no C7 H71 0.94(2) . . no C8 H81 0.94(2) . . no C12 H121 0.94(2) . . no C13 H131 0.937(18) . . no C17 H171 0.95(2) . . no C18 H181 0.93(2) . . no C21 H211 0.989(19) . . no C21 H212 0.968(18) . . no C22 H221 0.974(19) . . no C22 H222 0.95(2) . . no C23 H231 1.02(2) . . no C23 H232 0.991(19) . . no C24 H241 0.986(18) . . no C24 H242 0.957(17) . . no C25 H251 0.965(18) . . no C25 H252 0.988(19) . . no C26 H261 0.96(2) . . no C26 H262 0.99(2) . . no C27 H272 0.95(2) . . no C27 H271 0.98(2) . . no C28 H281 1.00(2) . . no C28 H282 1.00(2) . . no C29 H291 0.971(19) . . no C29 H292 0.980(18) . . no C30 H302 0.98(2) . . no C30 H301 0.965(19) . . no C31 H312 1.01(2) . . no C31 H311 0.95(2) . . no C32 H322 0.998(19) . . no C32 H321 0.950(18) . . no C33 H331 0.974(17) . . no C33 H332 0.989(18) . . no C34 H342 0.981(19) . . no C34 H341 0.97(2) . . no C35 H352 0.97(2) . . no C35 H351 0.969(19) . . no C36 H362 0.978(19) . . no C36 H361 0.953(17) . . no C41 C42 1.487(4) . . no C42 C431 1.468(4) . . no C44 C432 1.327(19) . . no C44 C45 1.47(3) . . no C41 H411 0.9806 . . no C41 H412 0.9809 . . no C41 H413 0.9796 . . no C45 H451 0.9788 . . no C45 H452 0.9793 . . no C45 H453 0.9805 . . no C51 C52 1.486(3) . . no C51 C53 1.489(3) . . no C52 H523 0.9807 . . no C52 H522 0.9796 . . no C52 H521 0.9808 . . no C53 H532 0.9806 . . no C53 H531 0.9798 . . no C53 H533 0.9807 . . no C431 H431 0.9795 . . no C431 H432 0.9796 . . no C431 H433 0.9799 . . no C432 H436 0.9799 . . no C432 H434 0.9795 . . no C432 H435 0.9800 . . no loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C22 S1 C23 99.84(8) . . . yes C26 S2 C27 98.32(9) . . . yes C30 S3 C31 97.50(8) . . . yes C34 S4 C35 97.08(8) . . . yes C1 N1 C4 110.43(13) . . . yes C6 N2 C9 110.89(13) . . . yes C11 N3 C14 110.45(12) . . . yes C16 N4 C19 111.15(13) . . . yes C4 N1 H1 124.5(14) . . . no C1 N1 H1 124.6(14) . . . no C6 N2 H2 126.1(14) . . . no C9 N2 H2 122.9(14) . . . no C14 N3 H3 125.5(12) . . . no C11 N3 H3 124.1(12) . . . no C19 N4 H4 124.8(13) . . . no C16 N4 H4 124.0(13) . . . no N1 C1 C2 106.78(13) . . . yes C2 C1 C20 131.14(14) . . . no N1 C1 C20 122.08(13) . . . yes C1 C2 C3 107.96(14) . . . no C2 C3 C4 107.67(14) . . . no N1 C4 C3 107.15(14) . . . yes C3 C4 C5 131.11(15) . . . no N1 C4 C5 121.29(14) . . . yes C4 C5 C6 107.89(13) . . . no C4 C5 C28 110.15(13) . . . no C6 C5 C25 108.38(13) . . . no C4 C5 C25 112.03(13) . . . no C25 C5 C28 109.66(14) . . . no C6 C5 C28 108.64(13) . . . no N2 C6 C7 106.54(14) . . . yes C5 C6 C7 133.14(15) . . . no N2 C6 C5 120.30(14) . . . yes C6 C7 C8 107.98(16) . . . no C7 C8 C9 107.88(16) . . . no N2 C9 C10 119.67(14) . . . yes C8 C9 C10 133.58(15) . . . no N2 C9 C8 106.71(14) . . . yes C9 C10 C11 107.81(12) . . . no C9 C10 C32 109.05(13) . . . no C11 C10 C29 111.01(13) . . . no C9 C10 C29 107.35(13) . . . no C11 C10 C32 111.54(13) . . . no C29 C10 C32 109.95(13) . . . no N3 C11 C10 121.70(14) . . . yes N3 C11 C12 106.82(13) . . . yes C10 C11 C12 131.21(15) . . . no C11 C12 C13 108.32(14) . . . no C12 C13 C14 107.75(14) . . . no N3 C14 C15 122.81(13) . . . yes C13 C14 C15 130.48(14) . . . no N3 C14 C13 106.65(13) . . . yes C14 C15 C16 109.87(12) . . . no C14 C15 C33 110.32(13) . . . no C16 C15 C33 109.09(12) . . . no C16 C15 C36 107.94(13) . . . no C14 C15 C36 110.46(13) . . . no C33 C15 C36 109.11(13) . . . no N4 C16 C17 106.52(14) . . . yes N4 C16 C15 122.17(13) . . . yes C15 C16 C17 131.25(14) . . . no C16 C17 C18 107.94(15) . . . no C17 C18 C19 107.76(15) . . . no C18 C19 C20 131.46(15) . . . no N4 C19 C18 106.63(14) . . . yes N4 C19 C20 121.89(14) . . . yes C1 C20 C21 109.41(12) . . . no C1 C20 C24 111.33(13) . . . no C19 C20 C21 108.62(13) . . . no C19 C20 C24 108.69(12) . . . no C21 C20 C24 108.80(13) . . . no C1 C20 C19 109.93(13) . . . no C20 C21 C22 114.96(13) . . . no S1 C22 C21 113.55(13) . . . yes S1 C23 C24 113.28(13) . . . yes C20 C24 C23 113.64(14) . . . no C5 C25 C26 114.46(15) . . . no S2 C26 C25 113.42(14) . . . yes S2 C27 C28 112.87(13) . . . yes C5 C28 C27 115.23(15) . . . no C10 C29 C30 115.34(14) . . . no S3 C30 C29 113.07(12) . . . yes S3 C31 C32 112.50(12) . . . yes C10 C32 C31 113.94(14) . . . no C15 C33 C34 113.28(14) . . . no S4 C34 C33 112.35(13) . . . yes S4 C35 C36 113.57(13) . . . yes C15 C36 C35 114.84(14) . . . no C1 C2 H21 125.8(11) . . . no C3 C2 H21 126.1(11) . . . no C2 C3 H31 126.0(12) . . . no C4 C3 H31 126.4(12) . . . no C6 C7 H71 124.9(12) . . . no C8 C7 H71 127.1(12) . . . no C7 C8 H81 127.4(13) . . . no C9 C8 H81 124.7(13) . . . no C11 C12 H121 126.3(12) . . . no C13 C12 H121 125.4(12) . . . no C12 C13 H131 125.3(11) . . . no C14 C13 H131 126.9(11) . . . no C16 C17 H171 125.9(12) . . . no C18 C17 H171 126.2(12) . . . no C17 C18 H181 127.5(13) . . . no C19 C18 H181 124.7(13) . . . no C20 C21 H211 107.2(11) . . . no C20 C21 H212 109.3(10) . . . no C22 C21 H211 109.7(11) . . . no C22 C21 H212 110.1(11) . . . no H211 C21 H212 105.1(15) . . . no S1 C22 H221 109.6(11) . . . no S1 C22 H222 103.6(13) . . . no C21 C22 H221 110.8(11) . . . no C21 C22 H222 111.1(13) . . . no H221 C22 H222 107.7(17) . . . no S1 C23 H231 104.5(12) . . . no S1 C23 H232 107.4(11) . . . no C24 C23 H231 110.3(12) . . . no C24 C23 H232 111.2(11) . . . no H231 C23 H232 109.9(16) . . . no C20 C24 H241 108.8(10) . . . no C20 C24 H242 108.6(10) . . . no C23 C24 H241 110.3(11) . . . no C23 C24 H242 107.8(10) . . . no H241 C24 H242 107.5(15) . . . no C5 C25 H251 105.7(11) . . . no C5 C25 H252 109.3(11) . . . no C26 C25 H251 109.8(11) . . . no C26 C25 H252 109.4(10) . . . no H251 C25 H252 107.9(15) . . . no S2 C26 H261 109.7(12) . . . no S2 C26 H262 106.4(12) . . . no C25 C26 H261 110.5(13) . . . no C25 C26 H262 110.1(12) . . . no H261 C26 H262 106.4(17) . . . no S2 C27 H271 108.5(12) . . . no S2 C27 H272 104.4(13) . . . no C28 C27 H271 111.7(12) . . . no C28 C27 H272 111.1(13) . . . no H271 C27 H272 108.0(17) . . . no C5 C28 H281 109.8(12) . . . no C5 C28 H282 107.1(11) . . . no C27 C28 H281 109.1(11) . . . no C27 C28 H282 109.2(11) . . . no H281 C28 H282 106.0(16) . . . no C10 C29 H291 106.5(11) . . . no C10 C29 H292 110.5(10) . . . no C30 C29 H291 108.8(11) . . . no C30 C29 H292 108.3(11) . . . no H291 C29 H292 107.1(15) . . . no S3 C30 H301 107.5(11) . . . no S3 C30 H302 105.5(12) . . . no C29 C30 H301 111.2(12) . . . no C29 C30 H302 110.7(11) . . . no H301 C30 H302 108.6(15) . . . no S3 C31 H311 104.8(13) . . . no S3 C31 H312 108.7(11) . . . no C32 C31 H311 110.0(13) . . . no C32 C31 H312 111.1(11) . . . no H311 C31 H312 109.5(17) . . . no C10 C32 H321 107.3(11) . . . no C10 C32 H322 108.9(11) . . . no C31 C32 H321 109.0(11) . . . no C31 C32 H322 109.8(11) . . . no H321 C32 H322 107.7(15) . . . no C15 C33 H331 109.7(10) . . . no C15 C33 H332 110.7(10) . . . no C34 C33 H331 108.7(10) . . . no C34 C33 H332 109.9(10) . . . no H331 C33 H332 104.2(14) . . . no S4 C34 H341 105.5(11) . . . no S4 C34 H342 109.5(11) . . . no C33 C34 H341 109.5(11) . . . no C33 C34 H342 110.2(11) . . . no H341 C34 H342 109.7(16) . . . no S4 C35 H351 108.8(12) . . . no S4 C35 H352 104.3(13) . . . no C36 C35 H351 110.1(11) . . . no C36 C35 H352 111.0(13) . . . no H351 C35 H352 108.9(17) . . . no C15 C36 H361 107.6(10) . . . no C15 C36 H362 109.4(11) . . . no C35 C36 H361 109.8(10) . . . no C35 C36 H362 108.1(11) . . . no H361 C36 H362 106.8(16) . . . no O40 C42 C41 121.3(3) . . . yes O40 C42 C431 122.5(3) . . . yes C41 C42 C431 116.2(2) . . . no O40 C44 C45 123.0(18) . . . yes O40 C44 C432 145(2) . . . yes C45 C44 C432 91.9(16) . . . no C42 C41 H411 109.43 . . . no C42 C41 H412 109.48 . . . no C42 C41 H413 109.44 . . . no H411 C41 H412 109.49 . . . no H411 C41 H413 109.50 . . . no H412 C41 H413 109.48 . . . no C44 C45 H452 109.52 . . . no C44 C45 H453 109.48 . . . no H451 C45 H452 109.55 . . . no H451 C45 H453 109.44 . . . no H452 C45 H453 109.36 . . . no C44 C45 H451 109.48 . . . no C52 C51 C53 117.6(2) . . . no O50 C51 C52 122.55(17) . . . yes O50 C51 C53 119.8(2) . . . yes C51 C52 H523 109.46 . . . no C51 C52 H521 109.49 . . . no C51 C52 H522 109.47 . . . no H522 C52 H523 109.50 . . . no H521 C52 H522 109.42 . . . no H521 C52 H523 109.48 . . . no C51 C53 H532 109.46 . . . no C51 C53 H531 109.47 . . . no H531 C53 H533 109.55 . . . no H532 C53 H533 109.46 . . . no H531 C53 H532 109.48 . . . no C51 C53 H533 109.41 . . . no H432 C431 H433 109.47 . . . no C42 C431 H433 109.49 . . . no C42 C431 H431 109.53 . . . no C42 C431 H432 109.45 . . . no H431 C431 H432 109.47 . . . no H431 C431 H433 109.43 . . . no C44 C432 H434 109.45 . . . no C44 C432 H435 109.54 . . . no C44 C432 H436 109.55 . . . no H434 C432 H435 109.41 . . . no H434 C432 H436 109.38 . . . no H435 C432 H436 109.50 . . . no # End of Crystallographic Information File